A large number of 1-(.beta.-aryl)ethyl-1H-imidazole antifungal and antibacterial agents are known, but the imidazole mercaptals of Formula I have not previously been reported in the literature.
U.S. Pat. No. 3,717,655 discloses 1-(.beta.-aryl)ethylimidazole ethers and amines of the formula ##STR3## in which R, R.sub.1 and R.sub.2 each are selected from hydrogen and (lower)alkyl; X is oxygen or NH; n is 1 or 2; Ar is phenyl [optionally substituted by halogen, (lower)alkyl or (lower)alkoxy], thienyl or halothienyl; Ar' is phenyl [optionally substituted by halogen (lower)alkyl, (lower)alkoxy; cyano, nitro or amino] or .alpha.-tetralyl; R' is hydrogen, methyl or ethyl; and R" is hydrogen or methyl; provided that (i) when X is NH, R is hydrogen; (ii) when Ar' is nitrophenyl or aminophenyl, X is oxygen and n is zero; (iii) when Ar' is .alpha.-tetralyl, X is NH and n is zero; and (iv) when X is oxygen and Ar' is phenyl, halophenyl, (lower)alkylphenyl, (lower)alkoxyphenyl or cyanophenyl, then n is other than zero; and therapeutically active acid addition salts thereof. The compounds are stated to have antifungal and antibacterial activity.
U.S. Pat. No. 4,055,652 discloses substituted 1-phenethylimidazoles of the formula ##STR4## wherein R is alkyl, alkenyl, aralkenyl, substituted aralkenyl, alkynyl, cycloalkyl, cycloalkyl alkyl, aralkyl, substituted aralkyl, aryl or substituted aryl, in which the substituents are selected from one or more of halogen, lower alkyl, lower alkoxy, trifluoromethyl, nitro and cyano, provided that the substituents on the substituted aryl may also be amino or acylamino; R.sup.1 is hydrogen, halogen, lower alkyl, lower alkoxy, trifluoromethyl, nitro, cyano, thiocyano or the group ##STR5## in which R.sup.2 is alkyl, cycloalkyl, aralkyl substituted aralkyl, aryl or substituted aryl, in which the substituents are selected from one or more halogen, lower alkyl, lower alkoxy, trifluoromethyl, nitro and cyano moieties; and m, n and p each are independently 0, 1 or 2, provided that m cannot be greater than n except when R.sup.1 is the group ##STR6## and R.sup.2 is aryl or substituted aryl; and the antimicrobial acid addition salts thereof. The compounds are stated to be useful antifungal, antibacterial and antiprotozoal agents.
U.S. Pat. No. 4,036,970 discloses .beta.,.gamma.-disubstituted propylimidazoles of the formula ##STR7## wherein R.sup.1 and R.sup.2 each are phenyl or benzyl which optionally contain on the phenyl rings one or more substituents selected from halogen, (lower)alkyl and trifluoromethyl; X and Y each are independently oxygen or sulfur, with the proviso that Y is not oxygen when R.sup.2 is phenyl or substituted phenyl; and the antimicrobial acid addition salts thereof. The compounds are stated to be useful as antifungal, antibacterial and antiprotozoal agents. The disclosure of U.S. Pat. No. 4,036,973 is substantially the same except that one of R.sup.1 and R.sup.2 must be alkyl or cyclohexylalkyl.
U.S. Pat. No. 3,796,704 discloses phenylimidazolylalkanyl derivatives of the formula ##STR8## in which R.sup.1, R.sup.2 and R.sup.3 each are selected from hydrogen and (lower)alkyl; R.sup.4 is hydrogen or an optionally substituted alkyl, alkenyl, alkynyl, aryl, aralkyl, aralkenyl, aralkynyl, aliphatic acyl, aromatic acyl or --R.sup.4' --O--R.sup.4" -- group, where R.sup.4' and R.sup.4" are saturated or unsaturated hydrocarbon groups, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, arylsulfonyl or a group of the formula ##STR9## in which Y is oxygen or sulfur, and R.sup.12 is an optionally substituted lower alkoxy, lower alkenyloxy, lower alkynyloxy, lower alkylmercapto, lower alkenylmercapto, lower alkynylmercapto, aryloxy, arylmercapto, amino, mono(lower alkyl-, lower alkenyl-, or lower alkynyl-)amino, monoarylamino, diarylamino, arylsulfonamido or --N(lower alkyl)--CO--NH--lower alkyl group; R.sup.5 is hydrogen or an alkyl, alkenyl, alkynyl or optionally substituted aryl radical; R.sup.6 and R.sup.7 each are selected from hydrogen or an optionally substituted alkyl, alkenyl, alkynyl or aryl radical; R.sup.8, R.sup.9 and R.sup.10 each are selected from hydrogen or a lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy or lower alkylthio group, or an electronegative group; X is oxygen, sulfur, --SO--, --SO.sub.2 --, --NH-- or an ##STR10## group, in which R" is hydrogen, lower alkyl, lower alkenyl or lower alkynyl; m is an integer of 1-6; and n is 0 or 1; and salts thereof. The compounds are stated to have antimycotic activity.
Published European patent application No. 1654 discloses substituted 1-phenethylimidazoles of the formula ##STR11## wherein R.sup.1, R.sup.2 and R.sup.3 are independently hydrogen or lower alkyl; R.sup.4 is hydrogen, lower alkyl or a cycloalkyl, benzyl or phenyl group which may contain one or more halogen, lower alkyl, lower alkoxy, lower alkylthio, phenyl, cyano, nitro or amino substituents, or a pyridyl group which is optionally substituted by halogen; R.sup.5 is nitro or lower alkyl; Ar is a phenyl group optionally substituted by one or more halogen, lower alkyl, lower alkoxy or cycloalkyl moieties, or a benzyl group optionally substituted by a substituent named under R.sup.4 ; X and Y are independently oxygen or sulfur; n is an integer of from 1 to 5; and p is 0, 1, 2 or 3; and pharmacologically acceptable acid addition salts thereof. The compounds are stated to be antimycotic and antibacterial agents.
U.S. Pat. No. 3,793,453 discloses 1-(.beta.-aryl)ethylimidazole ketals of the formula ##STR12## in which Z is --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH(CH.sub.3)-- or --CH(CH.sub.3)CH(CH.sub.3)--; and Ar is phenyl, halophenyl, dihalophenyl, trihalophenyl, (lower)alkylphenyl, (lower)alkoxyphenyl, nitrophenyl or 2-thienyl; and the therapeutically active acid addition salts thereof. The compounds are stated to have antibacterial and antifungal activity. U.S. Pat. No. 3,936,470 has a similar disclosure except that Ar may not be nitrophenyl or 2-thienyl; and Z is the group ##STR13## in which Ar.sup.2 is phenyl, naphthyl, halonaphthyl or phenyl having from 1 to 3 substituents selected from halo, loweralkyl, loweralkoxy, cyano, phenyl and benzyl; X is oxygen, sulfur or methylene; and n is 0 or 1.